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EP3885387A1 - Composés de polyaddition à base de polyisocyanate comportant des éléments structuraux d'iminoéther cyclique à cinq-chaînons - Google Patents

Composés de polyaddition à base de polyisocyanate comportant des éléments structuraux d'iminoéther cyclique à cinq-chaînons Download PDF

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Publication number
EP3885387A1
EP3885387A1 EP20165485.2A EP20165485A EP3885387A1 EP 3885387 A1 EP3885387 A1 EP 3885387A1 EP 20165485 A EP20165485 A EP 20165485A EP 3885387 A1 EP3885387 A1 EP 3885387A1
Authority
EP
European Patent Office
Prior art keywords
radicals
cycloaliphatic
polyaddition compound
aliphatic
isocyanate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP20165485.2A
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German (de)
English (en)
Inventor
Saskia BEUCK
Anne KUTZ
Hans-Josef Laas
Magdalena FLUEGEL
Michael Dornbusch
Philipp KNOSPE
Patrick Boehm
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
Original Assignee
Covestro Deutschland AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Covestro Deutschland AG filed Critical Covestro Deutschland AG
Priority to EP20165485.2A priority Critical patent/EP3885387A1/fr
Priority to EP21163845.7A priority patent/EP3885388A1/fr
Publication of EP3885387A1 publication Critical patent/EP3885387A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers

Definitions

  • the present invention relates to new polyisocyanate-based polyaddition compounds with five-membered cyclic iminoether structural elements, a process for the production of these polyaddition compounds and the use of these compounds for the production of polyurethane plastics.
  • the invention also relates to coating compositions containing the polyisocyanate-based polyaddition compounds and correspondingly coated substrates.
  • Five-membered cyclic imino ethers are known as oxazolines and were used in the past as starting materials for plastics, resins and adhesives. The preparation of polyimino ethers is described in various sources.
  • Oxazoline-functional reactive copolymers were manufactured by Nippon Shokubai Co. Ltd. under the name EPOCROS. commercialized based on technology from DOW Chemical Company USA. These polymers are used, for example, as water-based crosslinkers.
  • EPOCROS e.g., ethylene glycol dimethacrylate copolymer
  • the reaction of 2-oxazolines with carboxyl groups leads to the formation of stable amide bonds through ring opening, similar to the structures created by self-polymerization.
  • the reactivity of the oxazoline groups is also found towards epoxy groups and towards thiols and phenols.
  • EP 0 472 560 describes cyclic polyimino ethers resulting from the reaction of imino ethers with diisocyanates. Waxy, highly viscous substances are obtained. Five or six-membered cyclic compounds with isocyanate-reactive substituents in position 2 are used here as suitable imino ethers.
  • oxazoline-terminated polyurethanes based on polyurethane prepolymers, prepared from diisocyanates and polyols, and hydroxyl-functional imino ethers, known from EP 0 472 560 .
  • the highly viscous oxazoline-terminated polyurethane is produced in a two-stage synthesis.
  • the use of the compound produced as a heat-curable 1K system for use in coatings, adhesives and seals is also described.
  • US 5240744 describes a process for the production of coating compositions based on cyclic polyiminoethers. Bifunctional cyclic ones are preferred for use Polyimino ethers, which are produced from polyisocyanates and hydroxyl-functional monoimino ethers.
  • the coating compositions also contain various additives, monoimino ethers and / or lactones and are crosslinked in the heat via polymerization catalysts.
  • US 6306967 describes solid oxazoline-terminated, urethane-functional polyaddition compounds based on difunctional polyisocyanates and hydroxy- or amine-functional oxazoline derivatives.
  • oxazoline derivatives are used which are substituted at position 2 with a functional group.
  • the compounds described are used in the field of powder coatings.
  • the object of the present invention was therefore to produce new polyaddition compounds based on isocyanates and inexpensively available oxazoline derivatives with broad possibilities of structural diversity.
  • this object could be achieved by providing hydroxymethyl derivatives of the oxazolines which have isocyanate-reactive groups in position 4.
  • the present invention relates to polyaddition compounds which contain at least one structural element of the general formula (1) contain, in which the radicals R 1 and R 2 stand for identical or different radicals and are inert to isocyanate groups, linear or branched aliphatic, cycloaliphatic, optionally substituted aromatic or araliphatic radicals each with up to 18 carbon atoms and up to three or four heteroatoms can contain and in combination with one another can form a ring.
  • the invention also relates to a process for the production of these polyaddition compounds by reacting an oxazoline component A with an isocyanate component B, and the use of these polyaddition compounds for the production of polyurethane plastics, in particular of coating compositions for various substrates.
  • the polyaddition compounds according to the invention are prepared by reacting an oxazoline component A with an isocyanate component B.
  • Suitable oxazoline component A are any OH-functional 2-oxazolines of the general formula (2), in which R 1 and R 2 have the meaning described above for formula 1.
  • Aliphatic or araliphatic radicals R 1 and R 2 in formula 1 and 2 are, for example, those with 1 to 18 carbon atoms, such as.
  • Cycloaliphatic radicals R 1 and R 2 in formula 1 and 2 are, for example, those having 5 to 12 carbon atoms, such as.
  • Aromatic radicals R 1 and R 2 in formula 1 and 2 are, for example, those with 6 to 12 carbon atoms, such as. B. a phenyl, tolyl, xylyl, o-naphthyl, ⁇ -naphthyl, 4-diphenylyl, chlorophenyl, dichlorophenyl, trichlorophenyl, difluorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl , Diethylphenyl, isopropylphenyl, tert-butylphenyl, Dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, chloronaphthyl, ethoxynaphthyl, 2,6
  • radicals R 1 and R 2 in the general formula 1 or 2 preferably stand for identical or different linear or branched aliphatic or cycloaliphatic radicals with up to 18 carbon atoms which are inert towards isocyanate groups.
  • R 1 and R 2 are particularly preferably identical or different, linear aliphatic radicals which are inert towards isocyanate groups and have up to three carbon atoms.
  • R 1 and R 2 very particularly preferably each represent a CH 3 group.
  • Such starting compounds are known and can be prepared, for example, by reacting amino alcohols and acids or anhydrides in a cyclization reaction according to the following general reaction equation ( Bull. Soc. Chem. Belg., 1956, Vol 65, Issue 3-4, Page 377-402 ):
  • R 3 is preferably hydrogen.
  • the oxazoline component A is particularly preferably prepared using ⁇ '-dihydroxy-t-butylamine and acetic acid to give 2,4-dimethyl-4-hydroxymethyl-2-oxazoline.
  • Suitable isocyanate components B are any diisocyanates which can be obtained via phosgenation in the liquid or gas phase or in a phosgene-free route.
  • Preferred diisocyanates are those of the molecular weight range 140 to 400 g / mol with aliphatically, cycloaliphatically, araliphatically and / or aromatically bound isocyanate groups, such as. B.
  • 1,4-diisocyanatobutane 1,5-diisocyanatopentane (pentamethylene diisocyanate, PDI), 1,6-diisocyanatohexane (hexamethylene diisocyanate, HDI), 2-methyl-1,5-diisocyanatopentane, 1,5-diisocyanato-2,2- dimethylpentane, 2,2,4- or 2,4,4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3- and 1,4-diisocyanatocyclohexane, 1,3- and 1,4- Bis- (isocyanatomethyl) cyclohexane, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), 4,4'-diisocyanatodicyclohexylmethane
  • isocyanate components B are any di- and polyisocyanates with uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structure, accessible by modification of aliphatic, cycloaliphatic, araliphatic and / or aromatic diisocyanates, as described, for example, in J. Pract. Chem.
  • Isocyanate components B which are also suitable are any prepolymers which can be obtained by reacting any diisocyanates and / or any polyisocyanates with any polyol components. This also includes hydrophilically modified prepolymers and di- / polyisocyanates.
  • the actual modification reaction is generally followed by a further process step for separating off the unreacted excess monomeric diisocyanates.
  • This separation of monomers is carried out by processes known per se, preferably by thin-film distillation in a high vacuum or by extraction with suitable solvents which are inert towards isocyanate groups, for example aliphatic or cycloaliphatic hydrocarbons such as pentane, hexane, heptane, cyclopentane or cyclohexane.
  • diisocyanates, polyisocyanates and prepolymers of the type mentioned are preferably used as isocyanate components B which have a monomeric diisocyanate content of less than 1% by weight, preferably less than 0.5% by weight, particularly preferably less than 0.3% by weight.
  • the residual monomer contents are measured according to DIN EN ISO 10283: 2007-11 by gas chromatography using an internal standard.
  • Particularly preferred isocyanate components B for the process according to the invention are those of the type mentioned with exclusively aliphatically and / or cycloaliphatically bound isocyanate groups.
  • isocyanate components B are di- and / or polyisocyanates with exclusively aliphatically and / or cycloaliphatically bound isocyanate groups and with an isocyanurate and / or allophanate structure, most preferably those based on PDI, HDI, IPDI and / or 4,4 ' -Diisocyanatodicyclohexylmethane.
  • Di- and / or polyisocyanates and prepolymers which can be hydrophilically modified, are also suitable.
  • the polyaddition compound according to the invention is prepared by reacting the oxazoline components A with isocyanate components B at temperatures from 20 to 120 ° C., preferably from 30 to 100 ° C., particularly preferably from 50 to 90 ° C., while maintaining an equivalent ratio of NCO groups to NCO-reactive groups from 1: 1 to 1: 1.2.
  • the reaction takes place up to an NCO content of 0.1% by weight, and the course of the reaction can be followed by determining the NCO content.
  • the NCO content is preferably determined titrimetrically in accordance with DIN EN ISO 11909: 2007-05.
  • Suitable solvents are those which differ towards the reactive groups the starting components show inert.
  • Suitable solvents are, for example, the customary paint solvents known per se, such as. B.
  • the solvent C can be added to one or both of the reactants, the starting component A and / or the compound B.
  • the solvent C can be added to the mixture at any point in time during the metering in of the reactants or also afterwards, but preferably at the beginning of the metering.
  • the polyaddition compounds according to the invention are valuable starting components for polyurethane plastics, the curing of which takes place at temperatures of 100 to 220.degree. C., preferably at 120 to 200.degree. C., particularly preferably at 140 to 190.degree.
  • a catalyst is preferably added to accelerate the curing process.
  • Suitable catalysts are metal salts and chelates, salts of transition metals or semimetals, acids or bases.
  • the acids used can preferably be aromatic sulfonic acids, such as dodecylbenzenesulfonic acid, para-toluenesulfonic acid, trifluoromethanesulfonic acid and dinonylnaphthalenesulfonic acid, or sulfuric acid, acetic acid, trifluoroacetic acid or dibutyl phosphate.
  • N-substituted amidines such as 1,5-diazabicyclo [4.3.0] non-5-ene (DBN) and 1,5-diazabicyclo [5.4.0] undec-7-ene (DBU), can preferably be used as bases.
  • Tin chloride and zinc chloride are particularly preferably used.
  • the catalysts to be used are very particularly preferably dissolved in a solvent.
  • Particularly preferred catalyst solvents are, for example, alcohols, such as. B. ethanol or isopropanol, which can optionally also have a co-catalytic effect.
  • these catalysts are used, if at all, in an amount of from 0.001 to 5% by weight, preferably from 2.5 to 3.5% by weight, based on the total weight of the polyaddition compound.
  • Suitable substrates for the coatings formulated with the aid of the polyaddition compounds according to the invention are any substrates which are temperature-stable under the curing conditions, such as, for. B. metal, wood, glass, stone, ceramic materials, concrete, hard and flexible Plastics, textiles and leather, which can optionally also be provided with conventional primers before coating.
  • the color number was measured spectrophotometrically in accordance with DIN EN ISO 6271-2: 2005-03 using a LICO 690 spectral colorimeter from Lange, DE.
  • the non-volatile content (NFA) is measured in accordance with DIN EN ISO 3251.
  • 2,4-Dimethyl-4-hydroxymethyl-2-oxazoline made from 2-amino-2-methyl-1,3-propanediol and acetic acid.
  • the respective isocyanate component is introduced in the appropriate amount of solvent and heated to 60 ° C. At a temperature of 60 ° C., 2,4-dimethyl-4-hydroxymethyl-2-oxazoline is metered in over a period of 30 minutes. The reaction mixture is stirred at 60 ° C. until the theoretical NCO content of 0.0% by weight is reached.
  • the solvents xylene also abbreviated as “Xy” below
  • methoxypropyl acetate also abbreviated as “MPA” below
  • ethyl acetate also abbreviated as “EA” below
  • acetone also abbreviated as “Ac” below
  • the König pendulum damping was determined in accordance with DIN EN ISO 1522: 2007-04 on glass plates.
  • Table 2 below shows differently catalyzed and non-catalyzed coating formulations based on the polyaddition compounds according to the invention.
  • Table 2 Compositions of the paint mixtures. product Paint 1 (cf.) Paint 2 (cf.) Paint 3 (cf.) Paint 4 (cf.) Lac k 5 Lac k 6 Lac k 7 Lac k 8 Lac k 9 Lac k 10 Lac k 11 Lac k 12 NFA [%] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] [G] example 1 68.7% 10 10 10
  • Zinc chloride (in ethanol) 10.0% 2.0 6 2.0 2 2.1 0 2.0 8 Tin chloride (in ethanol
  • the paint systems 5, 6, 8, 9, 10, 11 and 12 achieve very good solvent resistance after stoving at 190 ° C. After baking at 160 ° C, lacquer 9, 10 and 12 in particular lead to very good solvent resistance. Lacquer systems 7 and 11 lead to significantly poorer resistances. A stoving temperature of 140 ° C leads to a decrease in solvent resistance in all systems.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
EP20165485.2A 2020-03-25 2020-03-25 Composés de polyaddition à base de polyisocyanate comportant des éléments structuraux d'iminoéther cyclique à cinq-chaînons Withdrawn EP3885387A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP20165485.2A EP3885387A1 (fr) 2020-03-25 2020-03-25 Composés de polyaddition à base de polyisocyanate comportant des éléments structuraux d'iminoéther cyclique à cinq-chaînons
EP21163845.7A EP3885388A1 (fr) 2020-03-25 2021-03-22 Composés de polyaddition à base de polyisocyanate pourvu d'éléments structuaux iminoéther cycliques à cinq chaînons destinés à la fabrication de matières plastiques polyuréthanes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP20165485.2A EP3885387A1 (fr) 2020-03-25 2020-03-25 Composés de polyaddition à base de polyisocyanate comportant des éléments structuraux d'iminoéther cyclique à cinq-chaînons

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EP3885387A1 true EP3885387A1 (fr) 2021-09-29

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EP20165485.2A Withdrawn EP3885387A1 (fr) 2020-03-25 2020-03-25 Composés de polyaddition à base de polyisocyanate comportant des éléments structuraux d'iminoéther cyclique à cinq-chaînons
EP21163845.7A Pending EP3885388A1 (fr) 2020-03-25 2021-03-22 Composés de polyaddition à base de polyisocyanate pourvu d'éléments structuaux iminoéther cycliques à cinq chaînons destinés à la fabrication de matières plastiques polyuréthanes

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* Cited by examiner, † Cited by third party
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